I have read the man pages for ifconfig and my wireless card wpi in my case and have a decent understanding of their contents. This morning while at Panera Bread getting some coffee I attempted to connect to their network and was able to do but only after resetting my nic to its default setting (i.e., -wpa, -nwid, -nwkey, etc, etc) I re-read ifconfig and wpi and could find no mention of this being a necessity. It is probably common knowledge so I apologize for my ignorance.

Onto my question - is there recommended reading in order to gain a greater understanding of how networks and nic's work within OpenBSD.

...is there recommended reading in order to gain a greater understanding of how networks and nic's work within OpenBSD

The first thing to recognize is that wired Ethernet networks are a mature & stable technology. The same isn't true about wireless. If you read through old threads both here & on the official misc@ mailing list, you will find a number of people commenting about various idiosyncrasies about the different wireless cards they use.

Wireless in the Open Source world (including Linux) is not plug-&-play. Some cards work, others don't, & many times users have to experiment to find out the peculiarities associated with the cards they have. Some work better than others. The problem is that the wireless vendors sell chipsets with the same model numbers, but varying degrees of crippled behavior. Likewise, new cards continue to come out where drivers don't exist yet. All of this is compounded by the fact that many vendors are very nervous about releasing specifications to their products. This hurts the Open Source world in its quest to write robust drivers.

As for documentation, network engineers have to digest lots of information. For general knowledge, go to a library & look at books by Douglas Comer. If you want to know what's going on at the code level, read the books by Richard Stevens. There aren't definitive wireless books yet, but you might want to look into the book market surrounding exams such as the CWNA, not that I am advocating that certifications are the best route, but digesting their material may be useful. Lastly, there are always the RFC's.

As I have said in other threads, the OpenBSD project is very small in comparison to other more publicly known projects. The developers like it this way. There will be gaps in the community & what documentation is made available by the project. Third-party information not affiliated with the project should be read with great skepticism because much of it is incomplete, out-of-date, or simply wrong. This is why being well-grounded is so very important to avoid getting snared in the OpenBSD world.

Network configuration in OpenBSD is not friendly to roaming users which is not to be seen as a critiscm. A secure OS just does not hook-up with the first available router

One option is to have two hostname.wpi0 interfaces, ie one with no wpa or wep and another with what ever encryption your home router users. Rename the one you want to use to hostname.wpi0 while renaming the additional interface as something like home.wpi0. Restart your network with
#sh /etc/netstart wpi0